Supplementary Material ON WATER REACTIVITY AND REGIOSELECTIVITY OF QUINONES IN C-N COUPLING WITH AMINES
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- Λαδων Ζάνος
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1 /CH13355_AC CSIRO 2014 Australian Journal of Chemistry 2014, 67(2), Supplementary Material ON WATER REACTIVITY AND REGIOSELECTIVITY OF QUINONES IN C-N COUPLING WITH AMINES Maximiliano Martínez-Cifuentes, A,C Graciela Clavijo-Allancan, A Carolina Di Vaggio- Conejeros, A Boris Weiss-Lopez B, Ramiro Araya-Maturana A,C A Departamento de Química Orgánica y Fisicoquímica, Faculta de Ciencias Químicas Y Farmacéuticas, Universidad de Chile, Casilla 233, Santiago 1, Chile. B Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile. C Corresponding author. mmartinez@ug.uchile.cl, raraya@ciq.uchile.cl
2 Table of contents S2 S2 S3-S56 General Information Synthetic General Procedure Characterization of Compounds and NMR spectra S3-S4 Compound 6 S5-S6 Compound 7 S7-S8 Compound 10 S9-S10 Compound 12 S11-S12 Compound 14 S13-S14 Compound 15 S15-S16 Compound 20 S17-S18 Compound 21 S19-S20 Compound 22 S21-S22 Compound 23 S23-S24 Compound 24 S25-S26 Compound 25 S27-S28 Compound 26 S29-S30 Compound 27 S31-S32 Compound 28 S33-S34 Compound 29 S35-S36 Compound 30 S37-S38 Compound 31 S39-S40 Compound 32 S41-S42 Compound 33 S43-S44 Compound 34 S45-S46 Compound 35 S47-S48 Compound 36 S49-S50 Compound 37 S51-S52 Compound 38 S53-S54 Compound 39 S55-S56 Compound 40 S3 B3LYP/6-31G (d,p) calculated structure and absolute energies 1. General Information Melting points were determined on a hot-stage apparatus and are uncorrected. The IR spectra were recorded on a FT-IR Bruker IFS 55 spectrophotometer from KBr discs; wave numbers are reported in cm H NMR and 13 C NMR spectra were obtained from a Bruker DRX-300 spectrometer (300 and 75 MHz respectively) in CDCl 3. Chemical shifts were recorded in ppm (δ) relative to TMS as an internal standard. J-values are given in Hz. Electron impact (IE) high resolution mass spectra were recorded on a Thermo Finnigan model MAT 95XP Mass Spectrometer and Maldi-TOF (TOF) high-resolution mass spectrum were recorded on a Waters LCT Premier XE Mass Spectrometer. S2
3 2. Synthetic General Procedure The reaction of quinone I with amine IV a was carried out using condition b. The reactions of quinones I and II with amines IV a and V a were carried out using conditions A and B, described below. The reactions of quinone II with amines IV b to IV g and V b to V n were carried out using conditions B. The synthesis of compounds II, 1 VIII-IX, XI, 2 XVI-XIX 3 have been previously described. A) Dissolving reactants in methylene chloride and stirring at room temperature overnight. B) Using water as the reaction medium and stirring at room temperature overnight. 3. Characterization of Compound and NMR spectra 2-Methyl-5-(4-phenyl-piperazin-1-yl)-[1,4]benzoquinone (VI) [1] R. Araya-Maturana, B.K. Cassels, T. Delgado-Castro, J.A.Valderrama, B.E. Weiss-López, Tetrahedron 1999, 55, 637. [2] S.C. Srivastava, U. Hornemann, Angew. Chem. 1976, 88, 87. [3] J.A. Valderrama, J.A. Ibacache, V. arancibia, J. Rodriguez, C. Theoduloz, Bioorg. Med. Chem. 2009, S3
4 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1024(C-N), 1643(C=O); 1 H NMR (CDCl 3, 300 MHz) δh 2.03 (d, 3H, J = 1.3 Hz), 3.32 (t, 4H, J = 5.3 Hz), 3.60 (t, 4H, J = 5.4 Hz), 5.79 (s, 1H), 6.43 (d, 1H, J = 1.5 Hz), 6.89 (d, 1H, J = 7.3 Hz), 6.93 (d, 2H, J = 8.5 Hz), 7.29 (t, 2H, J = 7.9 Hz), 13 C NMR (CDCl 3, 75 MHz) δc 15.60, 48.40, 48.66, , , , S4
5 129.22, , , , , , ; m/z (TOF) calcd. for C 17 H 18 N 2 O 2 H , found Methyl-6-(4-phenyl-piperazin-1-yl)-[1,4]benzoquinone (VII) S5
6 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1024(C-N), 1645(C=O); 1 H NMR (CDCl 3, 300 MHz) δh 2.03 (d, 3H, J = 1.6 Hz); 3.31 (q, 4H, J = 5.0 Hz, 7.1 Hz); 3.53 (q, 4H, J = 5.0 Hz, 6.9 Hz); 5.76 (d, 1H, J = 2.5 Hz); 6.47 (q, 1H, J = 7.3 Hz, 9.8 Hz); 6.92 (m, 3H); 7.28 (q, 2H, J = 7.5 Hz, 8.9 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 15.94, 48.64, 48.76, , , , , , , 150.6, , , ; m/z (TOF) calcd. for C 17 H 18 N 2 O 2 H , found S6
7 3,5-Dianilino-2-methylbenzo-1,4-quinone (X) S7
8 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1573(C=O), 3438(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 2.04 (s, 3H, J = 1.2 Hz), 6.17 (s, 1H), 6.90 (dd, 2H, J = 1.1 Hz, 8.4 Hz), 7.04 (m, 4H), 7.34 (m, 4H), 7.61 (s, 1H), 8.47 (s,1h); 13 C NMR (CDCl 3, 75 MHz) δc 13.79, 90.59, , , , , , , , , , , , , , , , ; m/z (TOF) calcd. for C 19 H 16 N 2 O 2 H , found S8
9 8,8-Dimethyl-3-(4-phenylpiperazin-1-yl)naphthalene-1,4,5(8H)-trione (XII) S9
10 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1233(C-N), 1694(C=O); 1 H NMR (CDCl 3, 300 MHz) δh 1.50 (s, 6H), 3.26 (t, 4H, J = 4.9), 3.55 (t, 4H, J = 5.3), 5.70 (s, 1H), 6.23 (d, 1H, J = 10.2 Hz), 6.69 (d, 1H, J = 10.2 Hz), 6.85 (t, 3H, J = 7.4 Hz), 7.22 (q, 2H, J = 7.3 Hz, J = 9.1 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 26.17, 38.69, 47.92, 48.74, , , , , , , , , , , , ; m/z (TOF) calcd. for C 22 H 22 N 2 O 3 Na , found Regiochemistry of compound 12 was assigned by 2D-NMR (HMBC, HSQC). S10
11 3-Anilino-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XIV) S11
12 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1699(C=O), 3250(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.59 (s, 6H), 6.19 (s, 1H), 6.30 (d, 1H, J = 10.0 Hz), 6.76 (d, 1H, J = 10.1 Hz), 7.21 (q, 3H, J = 6.4 Hz, 8.3 Hz), 7.33 (s, 1H), 7.40 (t, 2H, J = 8.1 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 26.70, 30.19, , , , , , , , , , , , , ; m/z (TOF) calcd. for C 18 H 15 NO 3 Na , found Regiochemistry of compound 14 was assigned by 2D-NMR (HMBC, HSQC).. S12
13 2-Anilino-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XV) S13
14 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1690(C=O), 3314(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.57 (s, 6H), 6.17 (s, 1H), 6.35 (d, 1H, J = 10.1 Hz), 6.75 (d, 1H, J = 10.1 Hz), 7.19 (m, 3H), 7.33 (s, 1H), 7.40 (t, 2H, J = 7.9 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 26.12, 37.25, , , , , , , , , , , , , , , ; m/z (TOF) calcd. for C 18 H 15 NO 3 H , found S14
15 3-(p-Toluidino)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXa) S15
16 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1601(C=O), 3243(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.58 (s, 6H), 2.34 (s, 3H), 6.12 (s, 1H), 6.28 (d, 1H, J = 10.2 Hz), 6.74 (d, 1H, J = 10.2 Hz), 7.08 (d, 2H, J = 8.3 Hz), 7.19 (d, 2H, J = 8.2 Hz), 7.29 (s, 1H); 13 C NMR (CDCl 3, 75 MHz) δc 20.89, 26.64, 39.12, , , , , , , , , , , , ; m/z (TOF) calcd. for C 19 H 17 NO 3 Na , found S16
17 3-(o-Toluidino)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXb) S17
18 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1610(C=O), 3318(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.60 (s, 6H); 2.26 (s, 3H); 5.82 (s, 1H); 6.32 (d, 1H, J = 10.1 Hz); 6.78 (d, 1H, J = 10.1 Hz); 7.16 (t, 1H, J = 3.8 Hz); 7.21 (dd, 1H, J = 2.2 Hz, 6.7 Hz); 7.24 (t, 1H, J = 1.9 Hz); 7.28 (m, 2H). 13 C NMR (CDCl 3, 75 MHz) δc 17.64, 26.70, 39.23, , , , , , , , , , , , , , , m/z (IE) calcd. for C 19 H 17 NO , found S18
19 3-(p-Chlorophenylamino)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXc) S19
20 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1697(C=O), 3261(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.59 (s, 6H), 6.13 (s, 1H), 6.30 (d, 1H, J = 10.1 Hz), 6.75 (d, 1H, J = 10.1 Hz), 7.14 (d, 2H, J = 8.8 Hz), 7.29 (s, 1H), 7.56 (d, 2H, J = 8.8 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 26.71, 39.19, , , , , , , , , , ; m/z (IE) calcd. for C 18 H 14 ClNO , found S20
21 3-(m-Chlorophenylamino)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXd) S21
22 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1694(C=O), 3245(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.58 (s, 6H), 6.20 (s, 1H), 6.30 (d, 1H, J = 10.1 Hz), 6.76 (d, 1H, J = 10.1 Hz), 7.09 (dd, 1H, J = 1.1 Hz, 8.1 Hz), 7.17 (dd, 1H, J = 1.8 Hz, J = 7.1 Hz), 7.21 (t, 1H, J = 1.9 Hz), 7.32 (t, 2H, J = 8.1 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 26.67, 39.15, , , , , , , , , , , , , , , , ; m/z (IE) calcd. for C 18 H 14 ClNO , found S22
23 3-(o-Chlorophenylamino)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXe) S23
24 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1682(C=O), 3115(N-H); 1H NMR (CDCl 3, 300 MHz) δh 1.58 (s, 6H), 6.14 (s, 1H), 6.30 (d, 1H, J = 10.2 Hz), 6.75 (d, 1H, J = 10.1 Hz), 7.14 (td, 1H, J = 1.6 Hz, 7.6 Hz), 7.30 (td, 1H, J = 1.3 Hz, 8.2 Hz), 7.37 (dd, 1H, J = 1.6 Hz, 8.0 Hz), 7.46 (dd, 1H, J = 1.3 Hz, 7.9 Hz), 7.59 (s, 1H); 13 C NMR (CDCl 3, 75 MHz) δc 26.64, 39.10, , , , , , , , , , , , , ; m/z (TOF) calcd. for C 18 H 14 ClNO 3 H found S24
25 3-(o-Bromophenylamino)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXf) S25
26 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1689(C=O), 3301(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.58 (s, 6H), 6.14 (s, 1H), 6.31 (d, 1H, J = 10.1 Hz), 6.76 (d, 1H, J = 10.1 Hz), 7.07 (m, 1H, J = 3.1 Hz, 6.0 Hz, 8.3 Hz ), 7.35 (t, 2H, J = 3.4), 7.56 (s, 1H), 7.64 (d, 1H, J = 8.5 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 17.64, 26.70, 39.23, , , , , , , , , , , , , , ; m/z (IE) calcd. for C 18 H 14 BrNO , found S26
27 3-(p-Bromophenylamino)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXg) S27
28 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1678(C=O), 3298(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.58 (s, 6H), 6.15 (s, 1H), 6.29 (d, 1H, J = 10.1 Hz), 6.76 (d, 1H, J = 10.1 Hz), 7.09 (d, 2H, J = 8.6 Hz), 7.28 (s, 1H), 7.52 (d, 2H, J = 8.8 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 27.12, 39.61, , , , , , , , , , , , , ; m/z (TOF) calcd. for C 18 H 14 NO 3 BrNa , found S28
29 3-(3,4-Dichlorophenylamino)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXg) S29
30 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1695(C=O), 3440(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.59 (s, 6H), 6.17 (s, 1H), 6.31 (d, 1H, J = 10.2 Hz), 6.77 (d, 1H, J = 10.0 Hz), 7.07 (dd, 1H, J = 2.6 Hz, 8.6 Hz), 7.29 (s, 1H), 7.34 (d, 1H, J = 2.6 Hz), 7.47 (d, 1H, J = 8.6 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 26.71, 39.19, , , , , , , , , , , , , , ; m/z (IE) calcd. for C 18 H 13 Cl 2 NO , found S30
31 3-(p-Methoxyphenylamino)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXh) S31
32 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1609(C=O), 3316(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.58 (s, 6H), 3.80 (s, 3H), 6.00 (s, 1H), 6.28 (d, 1H, J = 10.1 Hz), 6.74 (d, 1H, J = 10.1 Hz), 6.91 (d, 2H, J = 8.9 Hz), 7.13 (d, 2H, J = 8.9 Hz), 7.22 (s, 1H); 13 C NMR (CDCl 3, 75 MHz) δc 26.67, 29.63, 39.21, 55.48, , , , , , , , , , , , , ; m/z (TOF) calcd. for C 19 H 17 NO 4 H , found S32
33 3-(3,4-Dimethoxyphenylamino)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXi) S33
34 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1628(C=O), 3329(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.59 (s, 6H), 3.87 (s, 3H), 3.89 (s, 3H), 6.05 (s, 1H), 6.30 (d, 1H, J = 10.1 Hz), 6.70 (d, 1H, J = 2.3 Hz), 6.75 (d, 1H, J = 10.1 Hz), 6.77 (dd, 1H, J = 5.6 Hz, 10.1 Hz), 6.87 (d, 1H, J = 8.5 Hz), 7.22 (s, 1H); 13 C NMR (CDCl 3, 75 MHz) δc 26.73, 29.66, 39.25, 56.07, , , , , , , , , , , , , , , ; m/z (IE) calcd. for C 20 H 19 NO , found S34
35 3-(p-Acetylphenylamino)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXj) S35
36 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1693(C=O), 3425(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.58 (s, 6H), 2.58 (s, 3H), 6.30 (d, 1H, J = 10.0 Hz), 6.37 (s, 1H), 6.76 (d, 1H, J = 10.0 Hz), 7.29 (d, 2H, J = 8.6 Hz), 7.57 (s, 1H), 7.99 (d, 2H, J = 8.6 Hz); 13C NMR (CDCl 3, 75 MHz) δc 26.44, 26.64, 39.11, , , , , , , , , , , , , , ; m/z (TOF) calcd. for C 20 H 17 NO 4 H found S36
37 3-(o-Acetylphenylamino)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXk) S37
38 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1698(C=O), 3410(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.58 (s, 6H), 2.64 (s, 3H), 6.30 (d, 1H, J = 10.0 Hz), 6.49 (s, 1H), 6.74 (d, 1H, J = 10.1 Hz), 7.16 (td, 1H, J = 1.8 Hz, 6.7 Hz), 7.53 (q, 2H, J = 6.6 Hz, 8.1 Hz), 7.92 (dd, 1H, J = 1.0 Hz, 8.5 Hz), (s, 1H); 13 C NMR (CDCl 3, 75 MHz) δc 29.34, 31.90, 38.94, , , , , , , , , , , , , , ; m/z (TOF) calcd. for C 20 H 17 NO 4 H found S38
39 Ethyl 4-(5,5-dimethyl-1,4,8-trioxo-1,4,5,8-tetrahydronaphthalen-2- ylamino)benzoate (XXl) S39
40 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1698(C=O), 3410(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.38 (t, 3H, J = 7.1 Hz), 1.59 (s, 6H), 4.36 (q, 2H, J = 7.1 Hz), 6.39 (d, 1H, J = 10.1 Hz), 6.35 (s, 1H), 6.77 (d, 1H, J = 10.2 Hz), 7.26 (d, 2H, J = 8.7 Hz), 7.52 (s, 1H), 8.07 (d, 2H, J = 8.7 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 14.29, 26.67, 39.14, 61.09, , , , , , , , , , , , , , , , , ; m/z (TOF) calcd. for C 21 H 19 NO 5 H found S40
41 Ethyl 2-(5,5-dimethyl-1,4,8-trioxo-1,4,5,8-tetrahydronaphthalen-2- ylamino)benzoate (XXm) S41
42 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1703(C=O), 3435(N-H); 1 H NMR (CDCl 3, 300 MHz) δh 1.41 (t, 3H, J = 7.1 Hz), 1.59 (s, 6H); 6.23 (s, 6H), 4.41 (q, 2H, J = 7.1 Hz), 6.30 (d, 1H, J = 10.0 Hz), 6.47 (s, 1H), 6.74 (d, 1H, J = 10.1 Hz), 7.14 (dt, 1H, J = 1.4 Hz, 7.1 Hz), 7.51 (m, 2H), 8.07 (dd, 1H, J = 1.4 Hz, 7.8 Hz), (s, 1H); 13 C NMR (CDCl 3, 75 MHz) δc 14.22, 26.63, 38.97, 61.70, , , , , , , , , , , , , , , , ; m/z (TOF) calcd. for C 21 H 19 NO C 21 H 19 NO , found S42
43 3-(4-(2-Methoxyphenyl)piperazin-1-yl)-8,8-dimethylnaphthalene-1,4,5(8H)- trione (XXIa) S43
44 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1219(C-N), 1699(C=O); 1 H NMR (CDCl 3, 300 MHz) δh 1.55 (s, 6H); 3.16 (t, 4H, J = 4.8 Hz); 3.61 (t, 4H, J = 4.8 Hz); 3.86 (s, 3H); 5.75 (s, 1H); 6.27 (d, 1H, J = 10.1 Hz); 6.75 (d, 1H, J = 10.1 Hz); 6.87 (d, 1H, J = 8.0 Hz); 6.91 (d, 2H, J = 4.2 Hz); 7.03 (m, 1H); 13 C NMR (CDCl 3, 75 MHz) δc 26.18, 38.72, 48.36, 50.28, 55.42, , , , , , , , , , , , , , , ; m/z (TOF) calcd. for C 23 H 24 N 2 O 4 Na , found S44
45 3-(4-(3-Methoxyphenyl)piperazin-1-yl)-8,8-dimethylnaphthalene-1,4,5(8H)- trione (XXIb) S45
46 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1209(C-N), 1695(C=O); 1 H NMR (CDCl 3, 300 MHz) δh 1.54 (s, 6H); 3.30 (t, 4H, J = 4.8 Hz); 3.58 (t, 4H, J = 5.3 Hz); 3.77 (s, 3H); 5.74 (s, 1H); 6.27 (d, 1H, J = 10.1 Hz); 6.47 (m, 3H); 6.74 (d, 1H, J = 10.1 Hz); 7.17 (t, 1H, J = 7.96 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 26.11; 38.65; 47.77; 48.48; 55.13; ; ; ; ; ; ; ; ; ; ; ; ; ; ; m/z (TOF) calcd. for C 23 H 24 N 2 O 4 Na , found S46
47 3-(4-(2-Fluorophenyl)piperazin-1-yl)-8,8-dimethylnaphthalene-1,4,5(8H)- trione (XXIc) S47
48 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1232(C-N), 1700(C=O); 1 H NMR (CDCl 3, 300 MHz) δh 1.55 (s, 6H); 3.19 (t, 4H, J = 4.8 Hz); 3.59 (t, 4H, J = 5.1 Hz); 5.76 (s, 1H); 6.28 (d, 1H, J = 10.1 Hz); 6.74 (d, 1H, J = 10.2 Hz); 7.00 (m, 4H); 13 C NMR (CDCl 3, 75 MHz) δc 26.13; 38.65; 49.18; 50.09; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; m/z (TOF) calcd. for C 22 H 21 N 2 O 3 FNa , found S48
49 3-(4-(4-Fluorophenyl)piperazin-1-yl)-8,8-dimethylnaphthalene-1,4,5(8H)- trione (XXId) S49
50 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1207(C-N), 1695(C=O); 1 H NMR (CDCl 3, 300 MHz) δh 1.56 (s, 6H); 3.22 (t, 4H, J = 4.9 Hz); 3.59 (t, 4H, J = 5.3 Hz); 5.77 (s, 1H); 6.29 (d, 1H, J = 10.1 Hz); 6.76 (d, 1H, J = 10.1 Hz); 6.88 (m, 2H); 6.98 (m, 2H); 13 C NMR (CDCl 3, 75 MHz) δc 26.18; 38.73; 48.01; 49.91; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; m/z (TOF) calcd. for C 22 H 21 N 2 O 3 FNa , found S50
51 3-(4-(4-Nitrophenyl)piperazin-1-yl)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXIe) S51
52 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1230(C-N), 1296(N-O), 1563(N-O), 1701(C=O); 1 H NMR (CDCl 3, 300 MHz) δh 1.56 (s, 6H); 3.62 (m, 4H); 3.69 (m, 4H); 5.72 (s, 1H); 6.29 (d, 1H, J = 10.2 Hz); 6.77 (m, 3H); 8.15 (d, 2H, J = 9.34 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 26.21; 38.77; 45.84; 47.00; ; ; ; ; ; ; ; ; ; ; ; ; m/z (TOF) calcd. for C 22 H 21 N 3 O 5 Na , found S52
53 3-(4-(Pyridin-2-yl)piperazin-1-yl)-8,8-dimethylnaphthalene-1,4,5(8H)-trione (XXIf) S53
54 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1238(C-N), 1696(C=O); 1 H NMR (CDCl 3, 300 MHz) δh 1.54 (s, 6H); 3.59 (q, 4H, J = 4.2 Hz, 7.5 Hz); 3.70 (t, 4H, J = 4.2 Hz, 7.5 Hz); 5.72 (s, 1H); 6.27 (d, 1H, J = 10.3 Hz); 6.60 (d, 1H, J = 8.6 Hz); 6.64 (q, 1H, J = 5.5 Hz, 7.1 Hz); 6.74 (d, 1H, J = 10.2 Hz); 7.49 (m, 1H), 8.17 (dd, 1H, J = 1.1 Hz, 4.8 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 26.12; 38.67; 44.19; 47.51; ; ; ; ; ; ; ; ; ; ; ; ; ; ; m/z (TOF) calcd. for C 21 H 21 N 3 O 3 H , found S54
55 3-(4-(3,4-Dichlorophenyl)piperazin-1-yl)-8,8-dimethylnaphthalene-1,4,5(8H)- trione (XXIg) S55
56 Red powder; mp C; ν max (KBr)/cm (C-H ar ), 1228(C-N), 1695(C=O); 1 H NMR (CDCl 3, 300 MHz) δh 1.56 (s, 6H); 3.31 (t, 4H, J = 4.9 Hz); 3.60 (t, 4H, J = 4.9 Hz); 5.75 (s, 1H); 6.29 (d, 1H, J = 10.1 Hz); 6.74 (m, 2H); 6.94 (d, 1H, J = 2.9 Hz); 7.30 (d, 1H, J = 8.9 Hz); 13 C NMR (CDCl 3, 75 MHz) δc 26.21; 38.75; 47.60; 48.16; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; m/z (TOF) calcd. for C 22 H 20 Cl 2 N 2 O 3 H found S56
57 B3LYP/6-31G (d,p) calculated structure and absolute energies. Compound I E(RB3LYP)= au C C C C C C O O C H H H H H H Compound Ia E(B3LYP)= au C C C C C C O O C H H H H H H O H H O H H S57
58 Compound II E(B3LYP)= au C C C C C C H H C C H C C O O O C H H H C H H H H Compound IIa E(B3LYP)= au C C C C C C H H C C H C C O S58
59 O O C H H H C H H H H H O H H O H Compound IIb E(B3LYP)= au C C C C C C H H C C H C C O O O C H H H C H H H H H O H S59
60 H O H H O H Compound III E(RB3LYP)= au C C C C C C C C H C H O O C H H H C H H H N C O O C H H H Compound IIIa E(RB3LYP)= au C C C S60
61 C C C C C H C H O O C H H H C H H H N C O O C H H H H O H H O H Compound IV a E(B3LYP)= au C C C C C C N H H H H S61
62 H H H Compound IV a1 E(B3LYP)= au C C C C C C N H H H H H H H H O H Compound V a E(B3LYP)= C C C C C C N H H H H H C C C N C H S62
63 H H H H H H H H Compound V a1 E(B3LYP)= au C C C C C C N H H H H H C C C N C H H H H H H H H H O H H Compound VIII E(B3LYP)= au S63
64 C C C C C C O O C H H H H H N H C C C C H C H C H H H Compound VIIIa E(B3LYP)= au C C C C C C O O C H H H H H N H C S64
65 C C C H C H C H H H H O H H O H Compound IX E(B3LYP)= au C C C C C C O O H N H C C C C H C H C H H H H C H H H S65
66 Compound IXa E(B3LYP)= au C C C C C C O O H N H C C C C H C H C H H H H C H H H O H H H H O S66
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